Oxymetazoline

• 6-tert- butyl-3- (4,5- dihydro-1H- imidazol-2- ylmethyl) - 2,4- dimethylphenol (IUPAC)
• 2 - (2 ', 6' -dimethyl -3' -hydroxy- 4'-tert. -Butylbenzyl ) -2-imidazoline
• Latin: Oxymetazolinum

• R01AA05
• R01AB07
• S01GA04

Sympathomimetic

α1 -adrenoceptor agonist

181-183 ° C

Hydrochloride

Risk

0.8 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Oxymetazoline is a chemical compound from the group of imidazoline derivatives. It is used as a drug for decongestion of the nasal mucosa. As α -sympathomimetic it is an α1 -adrenoceptor agonist and causes contraction of smooth muscle. Thus, the locally situated blood vessels in the nose narrows ( vasoconstriction ) and the reduced blood flow can decongest mucous membranes. Oxymetazoline therefore found in nasal sprays, nasal ointments and nasal drop application.

In ophthalmology, the drug is used in eye drops for the treatment of non-infectious and allergic forms of conjunctivitis or pink eye (conjunctivitis).

Representation

Oxymetazoline was first synthesized by Wolfgang Fruhstorfer and Helmut Müller- Calgan at the company E. Merck AG Darmstadt on the basis of Xylometazolins as a starting basis. During the work it was found that the majority of new derivatives rather constipating acted as liberating in the nose. Some, however, showed the effect of Xylometazolins. From these we selected the on generic oxymetazoline -called derivative, which is characterized over the existing xylometazoline by a prolonged duration of action. Therefore, the means for on-board pharmacy the first moon landing in 1969 selected. The presentation can be achieved by the reaction of 2,6 -dimethyl -3-hydroxy -4- tert-butyl- benzyl cyanide with ethylenediamine in the presence of carbon disulfide and release of ammonia at 100 ° C for 48 hours. From the reaction product oxymetazoline is then recovered by repeated recrystallization from benzene in 75% yield.

Effects

Decades only was the effect of decongestant oxymetazoline is known which is obtained by a constriction of small blood vessels in the nasal mucosa. In recent years, in addition, a causal effect against rhinitis was detected. Oxymetazoline has a direct antiviral effect and reduced the expression of ICAM-1, a receptor for the human rhinovirus. This will find the rhinoviruses, the most common causative agent of acute rhinitis, less portals of entry into the nasal mucosa. The release of proinflammatory cytokines such as interleukins and TNF- α is inhibited in the presence of oxymetazoline. Inflammatory leukotrienes are suppressed by oxymetazoline, anti-inflammatory leukotrienes not. Oxymetazoline shortens the duration of acute rhinitis by a third.

Side effects

Prolonged use can lead to drying of the nasal mucosa and with an increased amount of blood the corresponding vessels accompanied ( congestion ). Therefore, a treatment period of seven days should not be exceeded. Occasionally, palpitations, or increased blood pressure. A use in pregnancy and lactation is recommended only on medical advice due to the systemic effect. For babies and toddlers oxymetazoline is well tolerated in age- appropriate dose.

Trade names

Dr. Cabana nose drops (A), Nasivin (D, A, CH), Vicks Sines (CH), Wick Sinex (D, A)